10409-54-8

Basic information

• Product Name: 2-BROMO-2-METHYLPROPIOPHENONE
• Synonyms: 2-BROMOISOBUTYROPHENONE;2-BROMO-2-METHYLPROPIOPHENONE;ALPHA-BROMOISOBUTYROPHENONE;A-BROMO-A-METHYLPROPIOPHENONE;A-BROMOISOBUTYROPHENONE;1-Propanone, 2-bromo-2-methyl-1-phenyl-;2-Bromo-2-methyl-1-phenyl-1-propanone;phenyl 2-bromo-2-propyl ketone
• CAS NO: 10409-54-8
• Molecular Formula: C₁₀H₁₁BrO
• Molecular Weight: 227.1
• EINECS: 233-879-6
• Mol File: 10409-54-8.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 146-148 °C30 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.35 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0188mmHg at 25°C
• Refractive Index: n20/D 1.5561(lit.)
• CAS DataBase Reference: 2-BROMO-2-METHYLPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-2-METHYLPROPIOPHENONE(10409-54-8)
• EPA Substance Registry System: 2-BROMO-2-METHYLPROPIOPHENONE(10409-54-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-27-37/39
• RIDADR: UN 2810 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 10409-54-8(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow liquid

InChI:InChI=1/C10H11BrO/c1-10(2,11)9(12)8-6-4-3-5-7-8/h3-7H,1-2H3

Synthetic route

phenyl isopropyl ketone (611-70-1) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With hydrogen bromide; bromine In dichloromethane for 4h;	100%
With bromine; acetic acid In tetrachloromethane	98%
With bromine In dichloromethane for 0.25h; Ambient temperature;	94%

2,2,5,5-tetramethyl-4-phenyl-3-imidazolin-1-oxyl (39753-69-0) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With bromine In chloroform for 1h;	96%
Multi-step reaction with 2 steps 1: aq. sodium nitrite, aq. hydrochloric acid / ethanol / 24 h 2: 90 percent / bromine / CHCl3 View Scheme

2-methyl-2-nitroso-1-phenyl-1-propanone (46175-01-3) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With bromine In chloroform	90%

C17H20O (2234-23-3) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With p-nitrobenzenesulfonamide; hydrogen bromide; oxygen; sodium nitrite In water; acetonitrile at 0 - 60℃; under 760.051 Torr; for 24.5h;	89%

1-bromo-2-methyl-1-phenyl-1-propene (5912-93-6) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With [hydroxy(tosyloxy)iodo]benzene; toluene-4-sulfonic acid In acetonitrile at 40℃; for 15h; Inert atmosphere;	80%

1-phenyl-2-methylpropane (538-93-2) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With hydrogen bromide; oxygen In water; ethyl acetate at 20℃; for 24h; Irradiation;	57%

2-bromoisobutyric acid bromide (20769-85-1) + benzene (71-43-2) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
With carbon disulfide; aluminium trichloride
With aluminum (III) chloride In dichloromethane at 20℃; for 1h;

(2-methyl-1-propenyl)-benzene (768-49-0) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
(i) NBS, aq. DMSO, (ii) CrO3, H2SO4; Multistep reaction;

(1,1-dimethyl-3-trimethylsilanyloxy-butyl)-(2-methyl-propenylidene)-amine (36867-23-9) + phenylmagnesium bromide → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
(i) THF, (ii) Br2, (iii) aq. oxalic acid; Multistep reaction;

phosphorus pentabromide (7789-69-7) + phenyl isopropyl ketone (611-70-1) + petroleum ether → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

rac-2-methyl-1-phenylpropan-1-ol (611-69-8) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: Cr2O3-H2SO4 2: petroleum ether; PBr5 View Scheme

benzene (71-43-2) → 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 1 h / 5 °C 2: sodium hypochlorite; hydrogen bromide / water / 13.5 h / 20 - 50 °C View Scheme

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → 2-azido-2-methyl-1-phenylpropan-1-one (118887-71-1)

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With sodium azide
With sodium azide In dimethyl sulfoxide at 20℃;	522 mg

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + potassium thioacetate (10387-40-3) → S-α,α-dimethylphenacyl thioacetate (14225-58-2)

Conditions	Yield
In N,N-dimethyl-formamide at 0℃; for 0.5h;	100%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + 4-cyanobenzaldehyde (105-07-7) → 3-(4-cyanophenyl)-3-hydroxy-2,2-dimethyl-1-phenyl-1-propanone

Conditions	Yield
With bismuth; zinc(II) fluoride In water-d2 for 16h;	98%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + thiophenol (108-98-5) → 2-methyl-1-phenyl-2-(phenylthio)propan-1-one (59919-11-8)

Conditions	Yield
With triethylamine In acetonitrile at 0℃;	97%
In ethanol

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → phenyl isopropyl ketone (611-70-1)

Conditions	Yield
With sodium dithionite; potassium carbonate; 1,1′-dioctyl-4,4′-bipyridinium In water; toluene at 35℃; for 3h;	96%
With bismuth; ammonium fluoride-hydrogen fluoride In water at 20℃; for 5h;	95%
With sodium dithionite In water; N,N-dimethyl-formamide for 5h; Ambient temperature;	91%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + di-tert-butyl 4-benzyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (401636-52-0) → 4-phenylpivalophenone (13031-08-8)

Conditions	Yield
With fac-tris(2-phenylpyridinato-N,C2')iridium(III); caesium carbonate In acetonitrile at 20℃; for 0.666667h; Mechanism; Reagent/catalyst; Solvent; Time; Schlenk technique; UV-irradiation; Inert atmosphere;	91%

methanol (67-56-1) + 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → methyl 2-methyl-2-phenylpropionate (57625-74-8)

Conditions	Yield
With silver hexafluoroantimonate for 2h; Ambient temperature; further reagent: Ag2CO3;	90%
With silver nitrate
With zinc dibromide at 115℃; for 5h; Addition; Rearrangement;

3-picoline-N-oxide (1003-73-2) + 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → nitrate d'α-(methyl-3 pyridinio-1 oxy)isobutyrophenone

Conditions	Yield
With silver nitrate In acetonitrile Ambient temperature;	90%

methanol (67-56-1) + 2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → 2-methoxy-3,3-dimethyl-2-phenyl-oxirane (13694-96-7)

Conditions	Yield
With sodium methylate for 0.166667h; Heating;	90%
With potassium carbonate for 2h; Ambient temperature; further reagent: silver carbonate;	86%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + 4-chlorobenzaldehyde (104-88-1) → 3-(4-chlorophenyl)-3-hydroxy-2,2-dimethyl-1-phenyl-1-propanone (75990-53-3)

Conditions	Yield
With water; zinc In diethyl ether	90%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + benzaldehyde (100-52-7) → 2,2-dimethyl-1,3-diphenyl-3-hydroxypropan-1-one (75990-52-2) + phenyl isopropyl ketone (611-70-1)

Conditions	Yield
With bismuth; zinc(II) fluoride In water-d2 for 12h;	A 90% B 5 % Spectr.
With bismuth; ammonium fluoride-hydrogen fluoride In water-d2 at 20℃; for 12h;

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + 3-Chlorobenzaldehyde (587-04-2) → 3-(3-Chloro-phenyl)-3-hydroxy-2,2-dimethyl-1-phenyl-propan-1-one (75990-54-4)

Conditions	Yield
With water; zinc In diethyl ether	88%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + N-cyano-N-phenyl-p-toluenesulfonamide (55305-43-6) → 2,2-dimethyl-3-oxo-3-phenylpropanenitrile (7391-73-3)

Conditions	Yield
With zinc In N,N-dimethyl-formamide at 20℃; for 2h; Reagent/catalyst; Inert atmosphere; Sealed tube;	88%

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) → 2,2,4,4-tetramethyl-1,5-diphenyl-3-thiapentane-1,5-dione (51110-88-4)

Conditions	Yield
With sodium sulfide In N,N-dimethyl-formamide for 2h; Ambient temperature;	87.1%
With sodium sulfide; Aliquat 336 In hexane; water for 6h; Ambient temperature; Yield given;

2-bromo-2-methyl-1-phenyl-propan-1-one (10409-54-8) + sodium methylate (124-41-4) → 2-methoxy-3,3-dimethyl-2-phenyl-oxirane (13694-96-7)

Conditions	Yield
In methanol for 3h;	87%
With diethyl ether

Upstream product

• 611-70-1 phenyl isopropyl ketone 
• 768-49-0 (2-methyl-1-propenyl)-benzene 
• 46175-01-3 2-methyl-2-nitroso-1-phenyl-1-propanone 
• 7789-69-7 phosphorus pentabromide 
• 538-93-2 1-phenyl-2-methylpropane 
• 2234-23-3 C₁₇H₂₀O 
• 5912-93-6 1-bromo-2-methyl-1-phenyl-1-propene 
• 71-43-2 benzene 
• 611-69-8 rac-2-methyl-1-phenylpropan-1-ol 
• 39753-69-0 2,2,5,5-tetramethyl-4-phenyl-3-imidazolin-1-oxyl 
• 36867-23-9 (1,1-dimethyl-3-trimethylsilanyloxy-butyl)-(2-methyl-propenylidene)-amine 
• 20769-85-1 2-bromoisobutyric acid bromide 

Downstream Products

• 109410-84-6 3,3-diethoxy-2,2-dimethyl-1-phenyl-propan-1-one 
• 53688-15-6 6-chloro-3,3-dimethyl-2-phenyl-3H-pyrido[2,3-b][1,4]thiazine 
• 61031-51-4 3-benzyl-4-hydroxy-5,5-dimethyl-4-phenyl-oxazolidin-2-one 
• 4381-14-0 9,9'-bixanthene 
• 126256-09-5 2-Methyl-1-phenyl-2-(9-xanthyl)-1-propanon 
• 126256-10-8 2-Methyl-1-phenyl-1-(9-xanthyl)-1-propanol 
• 611-70-1 phenyl isopropyl ketone 
• 1530-12-7 9,9'-bifluorenyl 
• 126256-03-9 2-(9-Fluorenyl)-2-methyl-1-phenyl-1-propanon 
• 126256-17-5 3,3-Dimethyl-4-oxo-2,4-diphenyl-2-(2-pyridyl)butyronitril 
• 126256-16-4 meso-2,3-Diphenyl-2,3-di-(2-pyridyl)succinodinitril 
• 126256-15-3 rac-2,3-Diphenyl-2,3-di-(2-pyridyl)succinodinitril 
• 126256-22-2 4-Hydroxy-2-(2-methoxyphenyl)-4-methyl-3-phenyl-2-pentennitril 
• 126256-08-4 2-(2-Methoxyphenyl)-3,3-dimethyl-4-oxo-4-phenylbutyronitril 

Relevant articles and documents

REACTION OF ALDEHYDES AND KETONES WITH t-BUTYL BROMIDE-DIMETHYL SULPHOXIDE

Reacting aldehydes and ketones with the "ButBr-Me2SO" system produces the corresponding α-bromoderivatives 2.In the case of ketones, where more than one regioisomer is possible, bromination is obtained exclusively at the more highly substituted α-position.With slight modifications of the reaction conditions (addition of Me2S, Me2SO) it is possible to obtain "in situ" formation of either dimethyl(2-oxo-phenylalkyl)sulphonium salts 3 or of α-methylthioderivatives 4.Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3h) during crystallization undergoes spontaneous resolution of the two enantiomers, as demonstrated by single crystal X-ray analysis and absolute configuration assignment.

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Synthesis and Spontaneous Resolution by Crystallization of R,S-(+/-)-Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium Bromide. X-Ray Structure and Absolute Configuration of the R-Enantiomer

R,S-(+/-)-Dimethyl(1-methyl-2-oxo-2-phenylethyl)sulphonium bromide (3a), obtained from 1-phenylpropanone by bromination with t-butyl bromide-dimethyl sulphoxide and further reaction with dimethyl sulphide, undergoes spontaneous resolution of its two enantiomers upon crystallization, as demonstrated by a single crystal X-ray analysis and assignment of absolute configuration (R).

β-KETO SULFIDE COMPOUND, PHOTOCURING AGENT AND PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THEM

To provide a β-keto sulfide compound, a photocuring agent and a photosensitive resin composition.SOLUTION: There are provided a compound represented by formula (1): (In the formula, Ring A represents a benzene ring or a naphthalene ring; R1 and R2 may be the same or different and each represents a hydrogen atom, an alkyl group which may have a substituent, and the like; R3 is an alkyl group, an acyl group, an alkoxy group, and the like; n represents an integer of 0 to 5; alternatively, R3 and R1 bonded to the carbon atom constituting Ring A may be bonded to each other to form a ring, and the ring may have a substituent; R4 represents an alkylene group which may have a hydroxy group; R5 represents an alkylene group; X represents an ester group and the like; Y represents a hydrogen atom or an organic group having a valency of 1 to 6;. p represents an integer of 1 to 6; q represents 0 or 1; with the proviso that when p represents 1, q represents 1 and Y represents a hydrogen atom, and that when p represents an integer of 2 to 6, q represents 0 or 1 and Y represents an organic group having a valency of 2 to 6), and a photocuring agent containing the compound, and a photosensitive resin composition containing them.SELECTED DRAWING: None

Access to α-Cyano Carbonyls Bearing a Quaternary Carbon Center by Reductive Cyanation

Reductive cyanation of tertiary alkyl bromides using electrophilic cyanating reagent and zinc reductant was developed, providing various α-cyano ketones, esters, and carboxamides containing a nitrile-bearing all-carbon quaternary center in good to excellent yields under mild reaction conditions. The corresponding reaction mechanism involving in situ generated organozinc reagent and reactivity distinction was elucidated by density functional theory computation.